Polyhydric alcohol ester of aliphatic carboxylic acids



Patented July 11, 1933 ASSTGNCE TO ELEBQTT LABORATORIES, OF A C RGGERAIDAIdfu, OF Elli-BANE ELLE/T NORTH CHIGAGQ, BILLING tartar on;

POLYHYDEIG ALCGHGL E ALEPI-ZA'IIC CABBGXYLIG ACIDS No Drawing.

The invention relates broadly to bactericides and has particularl to dowith a "j of substances which are especially appli ble as bactericidesand bacteriostatic ager combating acid-fast bacteria. The inv;

tion covered in this application may be considered an improvement overthat set forth and claimed in my (re-pending application on Bactericidesapplicable to acid-fast bactria, Serial No. 329 077, filed December 28.1928.

Chaulmo: g 'a oil, hydnocai iis wightia a. oil and related oils as wellas chaulmoog .c acid, and homologues of chaulmoogric acid and theirderivatives have long been. known to be effective in com :ating' certaindiseases such as leprosy, produced by ilCldfZtSb bacteria. The activityagainst the leper bacilli of all these products has generally beenattrilmted to the presence of the chaulmcogrie acid or a homologue.Recent d."-' c-.iveries have shown that a variety of other acids whichcontain other types of carbon rings are also eliective against suchacid-fast bacteria.

Further discoveries seem to demonstrate that a ring structure is notnecessary but that the number of carbon atoms, the molecular weight ofthe compounds, and the position of the carboxyl group in the chain areimportant factors in determining the bactericidal and bacteriostaticefficiency or" the products. Acids or derivatives of acids containingmore than 11 and less than 21 carbon atoms appear to be most efficient.particularly those containing 15 to 18 carbon atoms. The presence orabsence of a ring structure seems to be of minor importance.

As set forth in my co-pendin. application above referred to, I havefound surprisingly high. bactericidal and bacteriostatic efiiciency incertain aliphatic acids and their derivatives in which the carbonylgroup removed from the end of the chain, and that frequently theefiiciency is noticeably increased as the caboxyl group is placed nearerthe center. The highest eiiiciency seems to reside in those compoundswherein said group ttached to the middle carbon atom or to a carbon atomthat is near the middle of the molecule.

The present application relates to poly- Application filed January 21,1931. Serial No. 510,287.

hydric alcohol esters of acids which may be represented by the generalformula RCH (GOSH-DB, where- R and R are alkyl groups containing one ormore carbon atomsv and where the sum of the carbon atoms contained in31+ it in any single acid will total not less than 12 nor more than 21carbon atoms. The most effective esters are those rein the 20' ispresent contain a total of lo to 18 carbon atoms. Two of the most commonpolyhydric alcohols are ethylene glycol and glycerol,and'thcsesubstances are two of the most des rable of such alcohols formy purpose.

The esters covered by the previous statement essentially synthetic oilscorre spending very closely to natural'oils. These particular onescan'be used in place of chaulmoogra oil or the oil of hydnocarpuswio'htiana or oth of a similar character in the matmcnt of leprosy.

The substances covered in this application are somewhat less irritatingthan the products specifically referred to in my said co-pending'application. Hence, larger quantities thereof may be injected into thehuman or ganism.

Example 256 of di-heptyl acetic acid (3 mole iquivalents) and 31 (1 moleequivalent) of glycerol. are heated together in a roundbottomed flaskfitted with a condenser set for distillation, whereby the water which isobtained by heating the mixture may distill. The temperature of the bathis held at 225235 C. After heating about nine hours no more water iseliminated and the reaction is stopped. The reaction mixture is verydark brown and sometimes almost black.

The mixture is cooled and a 2-00. sample is titrated with 0.1 N sodiumhydroxide solution. To the main portion is then added sufiicient 5 percent sodium hydroxide solution in an amount equivalent to 20 per centmore than is sufiicient to neutralize the free 7 acid present. Themixture is then stirred vigorously for three hours at and allowed tosettle for another hour. Two layers separate, the bottom one containingthe soap and impurities, the top the light-brown glyceride. he latter iswashed four times with equal volumes of hot water and the last time isallowed to settle for one to two hours. The water is drawn oil and theoil dried by heating to 12O14:0O in vacuo for two to three hours. Theresulting glyceride cannot be distilled under any ordinary conditionswithout decomposition.

By this same. procedure, the ethylene glycolides and glycerides of thefollowing acids were prepared: di-n-pentyl acetic acid, n-butyln-hexylacetic acid, n-butyl-n-heptyl acetic acid, n-hexyl-n-amyl acetic acid,di-nhesyl acetic acid, n-butyl-n-octyl acetic acid,

n-hexyl-n-heptyl acetic acid, n-butyl'n-nonyl acetic acid, di-n-heptylacetic acid, n-lauryl ethyl acetic acid, n-propyl-n-undecyl acetic acid,n-heptyl-n-octyl acetic acid, di-n-octyl acetic acid, n-nonyl-n-heptylacetic acid, n-heptyl-n-decyl acetic acid, n-hexyl-nundecyl acetic acid,din-nonyl acetic acid and n-heptyl-lauryl acetic aci All of thesesubstances are obtained in the form of thick oils, brownish in color,odorless and essentially tasteless. They are readily converted by theaction of aqueous or alcoholic alkalies into glycol or glycerol and thesalts of the corresponding, aliphatic acids.

Various modifications and improvements coming within the spirit of myinvention will doubtless occur to those skilled in the art. Hence, I donot wish to be limited to the specific embodiments described or usesmentioned except as set forth in the appended claims, which are to beinterpreted as broad- 1y as the state of the art will permit.

I claim as my invention:

1. As a new composition of matter, especially useful as a bactericidalor bacteriostatic agent, a polyhydric alcohol ester of CPUCOOHlR, whereR and R are alkyl groups containing a total of not less than 12 or morethan 20 carbon atoms.

As a new composition of matter, especially useful as a bactericidal orbacteriostatic agent, a polyhydric alcohol ester of RCH(COOH)R, where Rand R are alkyl groups containing a total of not less than 15 or morethan 18 carbon atoms.

As a new composition of matter, especially useful as a bactericidal orbacteriostatic agent, an ethylene glycolide of RCH(COOH)R, where R and Rare alkyl groups containing a total of not less than 12 or more than 20carbon atoms.

4. As a new composition of matter, especially useful as a bactericidalor bacteriostatic agent, an ethylene glycolide of RCIHCOOHHI, where Rand R are alkyl e'roups containing a total of not less than 15 or morethan 18 carbon atoms.

5. As a new composition of matter, especially useful as a bactericidalor bacteriostatic agent, a glyceridc of RCH(COOH)R, where R- and R arealkyl groups containing a total of not less than 12 or more than 20carbon atoms.

6. As a new composition of matter, especially useful as a bactericidalor bacteriostatic agent, a glyceride of RCH (COOH) R, where R and R arealkyl groups containing a total of not less than 15 or more than 18carbon atoms.

ROGER ADAMS.

ll I;

